Blue light-emitting compounds, processes of preparing the same, and luminescent element including the same

Abstract

The present invention provides blue-light emitting compounds capable of emitting blue light at a high luminance for a long time upon the application of electric energy, processes of producing the compounds, and luminescent elements including the blue light-emitting compounds. One of the compounds according to the present invention is characterized by the chemical structure represented by formula (1).

1 . (canceled)  
   
   
       2 . A blue light-emitting compound having a chemical structure represented by formula (3):  
     
       
         
         
             
             
         
       
     
     wherein R 1  is a hydrogen atom, an alkyl group having 1 to 15 carbon atoms, a cycloalkyl group having 6 to 15 carbon atoms, or an aryl group represented by one of formulas (1-1) to (1-4), wherein two R 1 s may be the same or different from each other; and R 4  denotes a hydrogen atom, an aryl group represented by formula (3-1), or phenyl group, wherein four R 4 s may be the same or different from each other; 
 the formula (1-1) is:  
                     
 wherein X 1  is an alkyl group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, at least one hydrogen atom of which is replaced with a fluorine atom, or a hydrogen atom, and n denotes an integer of 1 to 5;  
 the formula (1-2) is:  
                     
 wherein X 1  means the same as the above; Y means an alkyl group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, at least one hydrogen atom of which is replaced with a fluorine atom, or a hydrogen atom; m denotes an integer from 1 to 3; q denotes an integer from 1 to 4; and X 1  and Y may be the same or different from each other;  
 the formula (1-3) is:  
                     
 wherein X 1 , Y, m and q denote the same as the above-defined, and X 1  and Y may be the same or different from each other;  
 the formula (1-4) is:  
                     
 wherein X 1 , Y, n, and q denote the same as those defined above, and X 1  and Y may be the same or different from each other; and  
 the formula (3-1) is:  
                     
 wherein R 5  denotes a hydrogen atom or an alkyl group with 1 to 5 carbon atoms.  
 
   
   
       3 . (canceled)  
   
   
       4 . (canceled)  
   
   
       5 . A process for producing the blue light-emitting compound represented by formula (3):  
     
       
         
         
             
             
         
       
     
     wherein R 1  is a hydrogen atom, an alkyl group having 1 to 15 carbon atoms, a cycloalkyl group having 6 to 15 carbon atoms, or an aryl group represented by one of formulas (1-1) to (1-4), wherein two R 1 s may be the same or different from each other; and R 4  denotes a hydrogen atom, an aryl group represented by formula (3-1), or phenyl group, wherein four R 4 s may be the same or different from each other; 
 the formula (1-1) is:  
                     
 wherein X 1  is an alkyl group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, at least one hydrogen atom of which is replaced with a fluorine atom, or a hydrogen atom, and n denotes an integer of 1 to 5;  
 the formula (1-2) is:  
                     
 wherein X 1  means the same as the above: Y means an alkyl group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, at least one hydrogen atom of which is replaced with a fluorine atom, or a hydrogen atom: m denotes an integer from 1 to 3; q denotes an integer from 1 to 4; and X 1  and Y may be the same or different from each other;  
 the formula (1-3) is:  
                     
 wherein X 1 , Y, m and q denote the same as the above-defined, and X 1  and Y may be the same or different from each other;  
 the formula (1-4) is:  
                     
 wherein X 1 , Y, n, and q denote the same as those defined above, and X 1  and Y may be the same or different from each other; and  
 the formula (3-1) is:  
                     
 wherein R 5  denotes a hydrogen atom or an alkyl group with 1 to 5 carbon atoms,  
 said process comprising halogenating a fluorene represented by formula (10) to produce an halogenated aromatic compound represented by formula (11), reacting the halogenated aromatic compound with triphenyl-phosphine to produce an organic phosphoric compound, and reacting the organic phosphoric compound with a carbonyl compound, wherein the formula (10) is:  
                     
 wherein R 1  denotes the same as that defined above; and  
 the formula (11) is:  
                     
 wherein R 1  denotes the same as that defined above, and “Hal” denotes a halogen atom.  
 
   
   
       6 . (canceled)  
   
   
       7 . A layered article including the blue light-emitting compound of  claim 2 .  
   
   
       8 . A layered article according to  claim 7  in a form of a luminescent element comprising a light-emitting layer including the blue light-emitting compound between a pair of electrodes.